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Information on EC 4.2.3.15 - myrcene synthase
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4.2.3.15 myrcene synthaseIUBMB Comments
A recombinant enzyme (also known as a monoterpene synthase or cyclase) from the grand fir (Abies grandis) requires Mn2+ and K+ for activity. Mg2+ is essentially ineffective as the divalent metal ion cofactor.
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Word Map
The enzyme appears in viruses and cellular organisms
Synonyms
AaTPS2, AcTPS2, AtTPS10, myrcene synthase, myrcene/(E)-beta-ocimene synthase, TPS10, TPS2, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
geranyl diphosphate = myrcene + diphosphate
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
elimination, C-O bond cleavage
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-
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PATHWAY SOURCE
PATHWAYS
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SYSTEMATIC NAME
IUBMB Comments
geranyl-diphosphate diphosphate-lyase (myrcene-forming)
A recombinant enzyme (also known as a monoterpene synthase or cyclase) from the grand fir (Abies grandis) requires Mn2+ and K+ for activity. Mg2+ is essentially ineffective as the divalent metal ion cofactor.
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CAS REGISTRY NUMBER
COMMENTARY
197462-59-2
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
geranyl diphosphate
(+)-limonene
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less than 5% of total hydrocarbon product
?
geranyl diphosphate
(-)-limonene
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less than 5% of total hydrocarbon product
?
geranyl diphosphate
(E)-beta-ocimene
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20% of total hydrocarbon product
?
geranyl diphosphate
2-carene
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less than 5% of total hydrocarbon product
?
geranyl diphosphate
myrcene + sabinene + linalool + limonene + diphosphate
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-
formation of 53.8% myrcene, 20.9% sabinene, 19.8% linalool and 5.5% limonene
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?
geranyl diphosphate
tricyclene
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less than 5% of total hydrocarbon product
?
geranyl diphosphate
myrcene + diphosphate
induced by stem wounding, enhances resistance to insects
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?
geranyl diphosphate
myrcene + diphosphate
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56% of total hydrocarbon product
?
geranyl diphosphate
myrcene + diphosphate
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products of Arabidopsis thaliana TPS10 are 56% beta-myrcene, 20% (E)-beta-ocimene, and less than 5% each of (+)-limonene, (-)-limonene, 2-carene, and tricyclene and an unknown monoterpene
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?
geranyl diphosphate
myrcene + diphosphate
the acyclic monoterpene myrcene is required for the production of the major aggregation pheromone component, ipsdienol
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-
?
geranyl diphosphate
myrcene + diphosphate
bifunctional enzyme: geranyldiphosphate synthase (EC 2.5.1.1)/myrcene synthase (EC 4.2.3.15). When the recombinant enzyme is incubated with dimethylallyl diphosphate and isopentenyl diphosphate as cosubstrates, the level of geranyl diphosphate formed is approximately tenfold higher than the level of myrcene formed. The data suggest that geranyl diphosphate is a free intermediate in myrcene production
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?
additional information
?
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terpenes produced from the wild-type and mutant enzymes are identical, showing low levels of beta-myrcene from AcTPS2-K514A
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?
additional information
?
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GC-MS analysis and identification of products from enzyme catalysis. Enzyme AaTPS2 produces a single product, beta-myrcene. No activity with farnesyl diphosphate or geranylgeranyl diphosphate
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-
?
additional information
?
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GC-MS analysis and identification of products from enzyme catalysis. Enzyme AaTPS2 produces a single product, beta-myrcene. No activity with farnesyl diphosphate or geranylgeranyl diphosphate
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-
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
additional information
?
-
-
terpenes produced from the wild-type and mutant enzymes are identical, showing low levels of beta-myrcene from AcTPS2-K514A
-
-
?
geranyl diphosphate
myrcene + diphosphate
induced by stem wounding, enhances resistance to insects
-
?
geranyl diphosphate
myrcene + diphosphate
the acyclic monoterpene myrcene is required for the production of the major aggregation pheromone component, ipsdienol
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-
?
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Mg2+
Mn2+
additional information
Mg2+
-
sequence contains conserved sequences R28(R)X8W and D321DXXD encoing putative Mg2+-binding sites
additional information
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wild-type AcTPS2 is significantly more active when KCl is absent from the activity buffer
additional information
although both Mg2+ and Mn2+ are able to support the catalytic activity of enzyme AaTPS2, an altered product spectrum is observed in the presence of Mn2+ for AaTPS2
additional information
-
although both Mg2+ and Mn2+ are able to support the catalytic activity of enzyme AaTPS2, an altered product spectrum is observed in the presence of Mn2+ for AaTPS2
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
additional information
Michaelis-Menten kinetics
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pI VALUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
bifunctional enzyme: geranyldiphosphate synthase/myrcene synthase
SwissProt
brenda
the tandem arginine motif RRX8W is conserved in the deduced protein of TPS10; bifunctional myrcene/(E)-beta-ocimene synthase
SwissProt
brenda
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
-
expression correlates well with floral volatile organic compounds emission in scented Alstroemeria genotypes
brenda
additional information
additional information
quantitative RT-PCR expression analysis in plants tissues. AaTPS2 exhibits the highest expression level in stem, and low expression in the other tissues
brenda
additional information
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quantitative RT-PCR expression analysis in plants tissues. AaTPS2 exhibits the highest expression level in stem, and low expression in the other tissues
brenda
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
evolution
the enzyme AaTPS2 belongs to the TPS superfamily, subclade TPS-b
metabolism
in Artemisia annua, three monoterpene synthases AaTPS2, AaTPS5, and AaTPS6, produce beta-myrcene, camphene, and 1,8-cineole as the major products, respectively, analysis of monoterpenes and sesquiterpenes produced by Artemisia annua plants, overview
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UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). TPS6_MAIZE
548
0
63731
Swiss-Prot
other Location (Reliability: 3)
MTS2_HUMLU
613
0
72214
Swiss-Prot
Chloroplast (Reliability: 2)
TPS11_MAIZE
548
0
63938
Swiss-Prot
other Location (Reliability: 3)
TPSA_ARATH
591
0
69279
Swiss-Prot
Chloroplast (Reliability: 4)
AGR4_AGRAE
342
0
38560
Swiss-Prot
other Location (Reliability: 1)
MYRS2_ARATH
598
0
69812
Swiss-Prot
Chloroplast (Reliability: 3)
MYRS_OCIBA
599
0
69963
Swiss-Prot
Chloroplast (Reliability: 1)
MYRS_QUEIL
597
0
69660
Swiss-Prot
Chloroplast (Reliability: 3)
TPSD2_ABIGR
627
0
72479
Swiss-Prot
Chloroplast (Reliability: 2)
TPS3_ANTMA
584
0
67339
Swiss-Prot
Mitochondrion (Reliability: 5)
TPS3_SOLLC
607
0
70652
Swiss-Prot
Chloroplast (Reliability: 3)
TPS26_MAIZE
627
0
70785
Swiss-Prot
Chloroplast (Reliability: 2)
TPS2_ANTMA
581
0
66705
Swiss-Prot
Chloroplast (Reliability: 4)
A0A396GHN4_MEDTR
290
0
34147
TrEMBL
Chloroplast (Reliability: 3)
A0A396GJF1_MEDTR
259
0
29971
TrEMBL
other Location (Reliability: 4)
A0A2I0B0T8_9ASPA
514
0
59423
TrEMBL
Mitochondrion (Reliability: 4)
A0A2G9GQ31_9LAMI
645
1
74958
TrEMBL
Chloroplast (Reliability: 4)
A0A072V9D0_MEDTR
591
0
69085
TrEMBL
Chloroplast (Reliability: 4)
A0A396JH72_MEDTR
431
0
50740
TrEMBL
Secretory Pathway (Reliability: 5)
A0A2G9G239_9LAMI
423
0
49307
TrEMBL
other Location (Reliability: 2)
A0A396GHK7_MEDTR
589
0
68985
TrEMBL
Chloroplast (Reliability: 4)
A0A396JDG4_MEDTR
167
0
19258
TrEMBL
Chloroplast (Reliability: 4)
A0A0B2SLK6_GLYSO
119
1
13796
TrEMBL
Secretory Pathway (Reliability: 2)
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
72500
calculated MW of recombinant protein expressed in Escherichia coli
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
K514A
-
AcTPS2 mutant, 90% reduction in monoterpene synthase activity compared to wild-type enzyme
K514S
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AcTPS2 mutant, presence of Ser is not able to rescue any of the activity lost after the removal of the Lys residue
additional information
additional information
the N-terminal signal peptide of AaTPS2 (46 amino acid residues) before RR motif is truncated and recombinantly expressed in Escherichia coli strain BL21(DE3)
additional information
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the N-terminal signal peptide of AaTPS2 (46 amino acid residues) before RR motif is truncated and recombinantly expressed in Escherichia coli strain BL21(DE3)
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
recombinant His-tagged enzyme without N-terminal signal peptide from Escherichia coli strain BL21(DE3) by nickel affinity chromatography
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli
expression in Escherichia coli
gene TPS2, cloning from a cDNA library, sequence comparisons and phylogenetic analysis and tree, quantitative RT-PCR expression analysis, recombinant expression of His-tagged enzyme without after removing the N-terminal plastid targeting sequence in Escherichia coli strain BL21(DE3)
mutated enzymes are generated using the QuickChange II site-directed mutagenesis kit. The PCR-based mutagenesis protocol is performed using pET200-D-TOPO harbouring the respective AcTPS2 cDNAs as template. The single-site mutant enzymes overexpressed in Escherichia coli.
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
AaTPS2 is upregulated after mechanical wounding, but treatments with phytohormones (salicylic acid, methyl jasmonate, and gibberellin) does not affect the expression of AaTPS2
expression correlates well with floral volatile organic compounds emission in scented Alstroemeria genotypes
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Bohlmann, J.; Steele C.L.; Croteau, R.
Monoterpene synthases from grand fir (Abies grandis): cDNA isolation, characterization, and functional expression of myrcene synthase, (-)-(4S)-limonene synthase, and (-)-(1S,5S)-pinene synthase
J. Biol. Chem.
272
21784-21792
1997
Abies grandis (O24474), Abies grandis
brenda
Bohlmann, J.; Martin, D.; Oldham, N.J.; Gershenzon, J.
Terpenoid secondary metabolism in Arabidopsis thaliana: cDNA cloning, characterization, and functional expression of a myrcene/(E)-beta-ocimene synthase
Arch. Biochem. Biophys.
375
261-269
2000
Arabidopsis thaliana (Q9ZUH4), Arabidopsis thaliana
brenda
Wise, M.L.; Rorrer, G.L.; Polzin, J.J.; Croteau, R.
Biosynthesis of marine natural products: isolation and characterization of a myrcene synthase from cultured tissues of the marine red alga Ochtodes secundiramea
Arch. Biochem. Biophys.
400
125-132
2002
Ochtodes secundiramea
brenda
Hosoi, M.; Ito, M.; Yagura, T.; Adams, R.P.; Honda, G.
cDNA isolation and functional expression of myrcene synthase from Perilla frutescens
Biol. Pharm. Bull.
27
1979-1985
2004
Perilla frutescens
brenda
Green, S.; Squire, C.J.; Nieuwenhuizen, N.J.; Baker, E.N.; Laing, W.
Defining the potassium binding region in an apple terpene synthase
J. Biol. Chem.
284
8661-8669
2009
Actinidia chinensis
brenda
Gilg, A.B.; Tittiger, C.; Blomquist, G.J.
Unique animal prenyltransferase with monoterpene synthase activity
Naturwissenschaften
96
731-735
2009
Ips pini (Q58GE8)
brenda
Aros, D.; Gonzalez, V.; Allemann, R.K.; Mueller, C.T.; Rosati, C.; Rogers, H.J.
Volatile emissions of scented Alstroemeria genotypes are dominated by terpenes, and a myrcene synthase gene is highly expressed in scented Alstroemeria flowers
J. Exp. Bot.
63
2739-2752
2012
Alstroemeria caryophyllaea
brenda
Ruan, J.X.; Li, J.X.; Fang, X.; Wang, L.J.; Hu, W.L.; Chen, X.Y.; Yang, C.Q.
Isolation and characterization of three new monoterpene synthases from Artemisia annua
Front. Plant Sci.
7
638
2016
Artemisia annua (A0A068L9J0), Artemisia annua
brenda
Kim, E.M.; Eom, J.H.; Um, Y.; Kim, Y.; Woo, H.M.
Microbial synthesis of myrcene by metabolically engineered Escherichia coli
J. Agric. Food Chem.
63
4606-4612
2015
Quercus ilex
brenda
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